The Significance of September in Making Dreams Come True

Why September trumps January for going after what you want

I was writing a friend’s birthday card last week when it occurred to me we’ve been friends for half our lives.

Seventeen years to be exact.

Granted that’s a significantly shorter duration than my oldest friendships stemming back to pre-school, it’s still pretty damn special.

Our seventeen-year bond stems back to my first move to Montreal, and a shared rite of passage as (budding) adults: Cegep (also known as pre-university college).

Dawson College in Montreal (the back entrance is the beautiful entrance)

I’d just graduated high school, and like most teenagers from the Laurentians—the vast mountain range where I grew up—I’d had to move to “the city” to continue my schooling.

Up until then, I’d been a frequent visitor to Montreal (since like my friend, my parents are “from the city” and 90% of our extended family is here.)

When I think back to September 2007, I remember moving into my first apartment with my older sister and our two best friends from “up North.”

I have to laugh at how crazy it seemed to my city friend—and her parents—that we were living on our own.

It seems crazy to me now too. Seventeen seems so young.

But of course, at the time, I thought I was so mature and knew so much more about life than I did.

As you can imagine, the experience humbled me the way any major change and character-building transformation does. That first big move on the cusp of adulthood laid the soil for all the other milestones I’ve hit in the latter half of my thirty-four-year-old life.

The Significance of September

September has always been my “Go” month. Nothing ushers in a “new year” like new stationery and the joy of writing on pages as crisp as the fall breeze with pens as colourful as the turn of leaves.

There’s something sacred about the head, hand, and heart connection when you capture dreams, goals, and aspirations in ink.

It’s always seemed more sincere than popping bottles of champagne and counting down from ten in unison (despite how fun that can be).

I embrace New Year’s sparkly nature, but as a friend once told me, “I’m a September girl” at heart.

September has more substance. That’s precisely why I have a disproportionate amount of September milestones.

September Milestones (From Ages 17 to 34)

This September marks…

• Seventeen years since I moved to Montreal for Cegep at age seventeen (happy “Champagne birthday” to me).

• Ten years since I fulfilled my dream of moving to London.

Bath was a favourite place to visit while in London

• Seven years since I moved to Sydney after Australia kept beckoning.

• Six years since I moved to Paris on a whim when my Australian visa sponsorship fell through. (I moved back to Montreal two years later.)

View of Paris from Créatures restaurant

• Three years since I quit my job to pursue my dream of self-employment.

• Three years since I started writing weekly because I felt compelled to share my journey.

• One year since I decided self-employment wasn’t working because despite all my efforts—and I gave it everything in me, believe me—I was lonely, lacking direction, and my finances were dwindling.

I’ve chased my dreams throughout the past seventeen years—the latter half of my life and the entirety of my adulthood.

The result of which is way too much hard-won wisdom to share in one post.

So I’ll limit today’s to two important gems.

Two Invaluable Gems of Wisdom From The Past 17 Years

1. Find what lights you up. You’ll be motivated to outperform.

Most of us know whether we belong in “T” or “F” territory in Myers–Briggs land. In other words, whether we tend to be led by our thoughts or our feelings. But regardless, everyone is ultimately led by their heart.

Attitude, effort, and hell, brute force, can only go so far when your heart isn’t in something.

Years ago, one of the best bosses and entrepreneurs I’ve ever worked for offered me advice I’ll never forget.

I was telling him about my dream of one day starting my own company and how my biggest barrier was coming up with the right idea.

The advice he gave me boils down to a simple formula:

energy + expertise = business opportunity

Here’s a paraphrased elaboration on his equation:

What fires you up so much that you can’t not teach it and to some extent, you already do (even if you don’t regard yourself as a “teacher”)?

Think of the topics you bring up over and over again in conversations and seek out like-minded people to discuss.

What are you inclined to post about on social media, whether it’s sharing your thoughts or resources you find valuable?

You ultimately want to figure out what “lights you up” because running a business is hard but as long as you’re doing what you love, you’ll always have that extra bit of motivation to outperform those who don’t.

When work blends with play and you’re making use of your natural talents, you’ll know you’re fulfilling your mission in life.

I spent years overthinking business ideas before I finally took a run at self-employment in September 2021. Meanwhile, I had the answers within me.

Had I embraced my heart space over my head space to figure out what lights me up sooner, who knows what opportunities I could’ve seized?

2. Test your options, then commit to the best one. You’ll be wiser for it.

When I think about my September milestones, I’m all the more adamant that Bill Burnett and Dave Evans distill incredible life advice in their best-selling book on how to apply Design Thinking to “build a well-lived, joyful life.”

Building on the adage that often what we think we want isn’t what makes us happy and thus it’s important to try things on for size the way you would a clothing garment, Burnett and Evans propose you prototype and test before going all in on any one option in life.

In their book, Designing Your Life, the authors share stories from an array of professionals who “always thought” they would become one thing but wound up pivoting when that thing turned out to be unfulfilling.

When it comes to “life design,” prototyping involves simulating future circumstances so you can collect feedback that will inform your next steps. The goal is to take off whatever rose-tinted glasses you're looking at the horizon with.

That’s not to say there’s an inherent negativity in the process. But prototyping and testing are meant to ground you by dissolving any illusions you have about what a future state “will be like.”

For every September milestone I’ve listed, for every adventure that followed, I can name an array of painful knockbacks that made their way into the story. Numerous inflection points sent me soaring upward, while others sent me crashing down to the point where I questioned why I put myself in that situation.

But of course, leading up to each milestone, I was naive. Take my move to London, for example. In my head, it was going to be one massive upward swing. But the reality was more of a rollercoaster ride.

One minute I was living my best life at glamorous events like The British Fashion Awards, Royal Ascot, or having high-tea at Harrods. The next, I was living a nightmare dealing with a flooded apartment, struggling to make ends meet, and adapting to people constantly coming and going in a bustling city.

Day after day I had to push myself out of my comfort zone to meet new people and try new things. But those experiences were a catalyst for the woman I am today.

Had I never pursued my dream of living in London, I would’ve spent the next few decades deluding myself about how “perfect” it would’ve been, wondering how different my life might be had I worked up the courage to go.

Thankfully, I made it happen. I put my dream to the “test” and despite some incredibly challenging moments, the highs massively outweighed the lows.

I met people from all over the world. I visited historical landmarks like Stonehenge. And most importantly, I learned how to rely on myself, and to ask others for guidance along the way. 

In the end, I stayed in London for a second year, and my experience gave me the confidence to pursue subsequent dreams of moving to Sydney and Paris, before resettling in Montreal.

Now, having “prototyped and tested” life as a Londoner, Parisian, and Sydneysider, I know that while each city made a fantastic home at different stages in my life, my ultimate home is Montreal.

And now I have the opportunity to integrate what I’ve learned and the friendships I’ve developed in each place into my life in Canada, making it all the richer.

Something to think about

I have a disproportionate amount of September milestones. I’m convinced it’s because September has more substance than January in propelling people toward their dreams.

For those of us in the Northern Hemisphere, I imagine it has to do with “starting a new grade” year after year around this time. From early childhood (I mentioned pre-school earlier), we associate September with levelling up.

I clearly never lost that momentum.

I hope you haven’t either.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. I have a September 2024 game plan to make another dream come true. Stay tuned for updates.